Im confused and contemplating on what to do.  

An owner-led company might take those risks, but as an employee-owned company it's harder to contemplate. 

I find myself contemplating the idea of finding mentors or coaches to help me get on my feet.

@Phil AveryConsidering your financial situation and the current market conditions, each of the options you're contemplating has its own merits.Given your inclination to begin with a significant amount of equity, option 1 may be a good fit for your objectives.

I am wondering because I am contemplating using the short term rental loophole this year. 

@Jessie Dillon Yocheved was contemplating specific performance, not suing for lost opportunity. 

That's all you are doing with your contemplated entity structure as they will be more inclined to want to see what's hidden leading to an even more thorough and invasive discovery process. 

Best to seek counsel from your attorney and tax professional but if you are going to insist on saving a few dollars, best to provide more specifics on the type of partnership you are contemplating so you can get your hands on something that's remotely relevant. 

It seems that you are contemplating built and sell. 

For those out there contemplating jumping in or are still early on in their REI journey.